Acetic Anhydride → 4-Methylmorpholine-2,6-dione
Reaction equation
[CH3:1][N:2]([CH2:7][C:8]([OH:10])=[O:9])[CH2:3][C:4]([OH:6])=O.C(OC(=O)C)(=O)C>>[CH3:1][N:2]1[CH2:3][C:4](=[O:6])[O:10][C:8](=[O:9])[CH2:7]1Participants
3
Conditions
- Temperature
- 165 °C
Procedure
A mixture of 2,2′-(methylazanediyl)diacetic acid (500 mg, 3.40 mmol) and acetic anhydride (5 mL) was stirred at 165° C. for 30 min. The reaction mixture was concentrated under reduced pressure to give 4-methylmorpholine-2,6-dione as a crude product. The obtained crude product was dissolved in THF (10 mL), and p-aminobenzonitrile (401 mg, 3.40 mmol) was added thereto. The mixture was heated with reflux for 22 hr, and concentrated under reduced pressure to give 2-((2-((4-cyanophenyl)amino)-2-oxoethyl)(methyl)amino)acetic acid (467 mg, 56%) as a pale-brown powder.
Workup
- concentrationThe reaction mixture was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-f64e90e3f7524f40b24eaff3bbfc6dfb
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09120776B2
Reaction notes
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